Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
- Autores
- la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor
- Año de publicación
- 2012
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.
Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lemrová, Barbora. Palacky University; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University Of Notre Dame-Indiana; Estados Unidos - Materia
-
Iminium Chemistry
Bisheterocycles
Solid-Phase Synthesis
Regioselectivity - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/21572
Ver los metadatos del registro completo
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Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesisla Venia, AgustinaLemrová, BarboraKrchnak, ViktorIminium ChemistryBisheterocyclesSolid-Phase SynthesisRegioselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Lemrová, Barbora. Palacky University; República ChecaFil: Krchnak, Viktor. Palacky University; República Checa. University Of Notre Dame-Indiana; Estados UnidosAmerican Chemical Society2012-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/21572la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor; Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis; American Chemical Society; ACS Combinatorial Science; 15; 1; 12-2012; 59-722156-8952CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/co300125minfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co300125minfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:40:21Zoai:ri.conicet.gov.ar:11336/21572instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:40:21.495CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
title |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
spellingShingle |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis la Venia, Agustina Iminium Chemistry Bisheterocycles Solid-Phase Synthesis Regioselectivity |
title_short |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
title_full |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
title_fullStr |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
title_full_unstemmed |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
title_sort |
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis |
dc.creator.none.fl_str_mv |
la Venia, Agustina Lemrová, Barbora Krchnak, Viktor |
author |
la Venia, Agustina |
author_facet |
la Venia, Agustina Lemrová, Barbora Krchnak, Viktor |
author_role |
author |
author2 |
Lemrová, Barbora Krchnak, Viktor |
author2_role |
author author |
dc.subject.none.fl_str_mv |
Iminium Chemistry Bisheterocycles Solid-Phase Synthesis Regioselectivity |
topic |
Iminium Chemistry Bisheterocycles Solid-Phase Synthesis Regioselectivity |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile. Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Lemrová, Barbora. Palacky University; República Checa Fil: Krchnak, Viktor. Palacky University; República Checa. University Of Notre Dame-Indiana; Estados Unidos |
description |
A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile. |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-12 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/21572 la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor; Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis; American Chemical Society; ACS Combinatorial Science; 15; 1; 12-2012; 59-72 2156-8952 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/21572 |
identifier_str_mv |
la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor; Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis; American Chemical Society; ACS Combinatorial Science; 15; 1; 12-2012; 59-72 2156-8952 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1021/co300125m info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co300125m |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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1846082894677671936 |
score |
13.22299 |